1. Field of the Invention
The present invention relates to uracil compounds and herbicidal compositions comprising them as active ingredients.
2. Description of Related Art
Although numerous herbicides have been commercialized, the weeds that need to be controlled are varied and their germination lasts over a long period. Accordingly, new herbicides are needed that have a higher herbicidal activity and a wide herbicidal spectrum but do not cause phytotoxicity on crops.
U.S. Pat. No. 4,859,229 and WO 95/32952 disclose that certain kinds of phenyluracil compounds have an herbicidal activity. However, uracil compounds having improved herbicidal performance are desired.
The purpose of the invention is to provide compounds having excellent performance as a herbicide.
As the result of extensive studies seeking compounds having excellent performance as a herbicide, the present inventors have found that uracil compounds represented by the following formula [L] have an excellent performance as a herbicide and have completed the invention. Accordingly, the invention provides uracil compounds (hereinafter, referred to as the present compound) represented by the formula [L]: 
wherein A1 represents amino or C1-C3 alkyl, A2 represents C1-C3 haloalkyl, X represents hydrogen or halogen, Y represents halogen,
R1 represents xe2x80x94OR21, xe2x80x94ON(R22)R23, xe2x80x94ONxe2x95x90C(R24)R25, xe2x80x94SR26, xe2x80x94N(R27)R28, xe2x80x94N(R29)OR30, xe2x80x94N(R31)SO2R32 or xe2x80x94N(R33)N(R34)R35,
(wherein R21 represents hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, C3-C6 cycloalkyl, carboxy C1-C6 alkyl, C1-C6 alkoxycarbonyl C1-C6 alkyl, C3-C6 alkenyloxycarbonyl C1-C6 alkyl, C3-C6 alkynyloxycarbonyl C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkyl, benzyl or phenyl (the benzyl and phenyl maybe substituted with one or more of halogen, C1-C6 alkyl and C1-C6 alkoxy) or tetrahydrofuryl (the tetrahydrofuryl may be substituted with one or more of hydroxy, C1-C6 alkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy and C1-C6 alkylcarbonyloxy),
R22 and R23 independently represent hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 alkynyl or benzyl (the benzyl may be substituted with one or more of halogen, C1-C6 alkyl and C1-C6 alkoxy),
R24 and R25 independently represent hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, benzyl or phenyl (the benzyl and phenyl may be substituted with one or more of halogen, C1-C6 alkyl and C1-C6 alkoxy),
R26 represents hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, C3-C6 cycloalkyl, carboxy C1-C6 alkyl, C1-C6 alkoxycarbonyl C1-C6 alkyl, C3-C6 alkenyloxycarbonyl C1-C6 alkyl, C3-C6 alkynyloxycarbonyl C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkyl, benzyl or phenyl (the benzyl and phenyl maybe substituted with one or more of halogen, C1-C6 alkyl and C1-C6 alkoxy),
R27 represents hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, C3-C6 cycloalkyl, carboxy C1-C6 alkyl, C1-C6 alkoxycarbonyl C1-C6 alkyl, C3-C6 alkenyloxycarbonyl C1-C6 alkyl, C3-C6 alkynyloxycarbonyl C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkyl, benzyl or phenyl (the benzyl and phenyl maybe substituted with one or more of halogen, C1-C6 alkyl and C1-C6 alkoxy),
R28 represents hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, benzyl or phenyl (the benzyl and phenyl may be substituted with one or more of halogen, C1-C6 alkyl and C1-C6 alkoxy),
R29 and R30 independently represent hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 alkynyl or benzyl (the benzyl may be substituted with one or more of halogen, C1-C6 alkyl and C1-C6 alkoxy),
R31 represents hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, benzyl or phenyl (the benzyl and phenyl may be substituted with one or more of halogen, C1-C6 alkyl and C1-C6 alkoxy),
R32 represents C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, benzyl or phenyl (the benzyl and phenyl may be substituted with one or more of halogen, C1-C6 alkyl and C1-C6 alkoxy),
R33, R34 and R35 independently represent hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, benzyl or phenyl (the benzyl and phenyl may be substituted with one or more of halogen, C1-C6 alkyl and C1-C6 alkoxy),
R2, R3, R4 and R5 independently represent hydrogen or C1-C3 alkyl.
The present invention also provides a herbicidal composition comprising, as an active ingredient, such an uracil compound.
In the present invention, stereoisomers of the uracil compounds may exist with respect to a double bond or an asymmetric carbon atom. It will be appreciated that the present invention includes individual stereoisomers of the uracil compounds, as well as mixtures thereof.
In the present invention:
With regard to A1, C1-C3 alkyl represents methyl, ethyl, propyl or isopropyl.
With regard to A2, C1-C3 haloalkyl includes trifluoromethyl, difluoromethyl, fluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trichloromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, 1,1-difluoroethyl, 1-fluoroethyl, 2-fluoroethyl and the like.
With regard to R2, R3, R4 and R5, C1-C3 alkyl represents methyl, ethyl, propyl or isopropyl.
With regard to R21, C1-C6 alkyl includes methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl (hereinafter xe2x80x9ctxe2x80x9d means xe2x80x9ctertiaryxe2x80x9d, unless noted otherwise), pentyl, isopentyl, neopentyl, hexyl and the like;
C1-C6 haloalkyl includes fluoromethyl, chloromethyl, bromomethyl, trifluoromethyl, chloroethyl and the like;
C3-C6 alkenyl includes allyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-butenyl, 3-butenyl and the like;
C3-C6 alkynyl includes propargyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 2-butynyl, 3-butynyl and the like;
C3-C6 cycloalkyl includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like;
carboxy C1-C6 alkyl includes carboxymethyl, 1-carboxyethyl, 1-carboxy-1-methylethyl and the like;
C1-C6 alkoxycarbonyl C1-C6 alkyl includes methoxycarbonylmethyl, ethoxycarbonylmethyl, 1-methoxycarbonylethyl,
1-methoxycarbonyl-1-methylethyl, 1-ethoxycarbonylethyl and the like;
C3-C6 alkenyloxycarbonyl C1-C6 alkyl includes allyloxycarbonylmethyl, 1-allyloxycarbonylethyl, 2-allyloxycarbonylethyl, 1-allyloxycarbonyl-1-methylethyl and the like;
C3-C6 alkynyloxycarbonyl C1-C6 alkyl includes propargyloxycarbonylmethyl, 1-propargyloxycarbonylethyl, 2-propargyloxycarbonylethyl, 1propargyloxycarbonyl-1-methylethyl and the like;
C1-C6 alkoxy C1-C6 alkyl includes 2-methoxyethyl, 2-ethoxyethyl, 3-methoxypropyl and the like;
benzyl which may be substituted with one or more of halogen, C1-C6 alkyl and C1-C6 alkoxy includes benzyl, 4-chlorobenzyl, 4-methylbenzyl and the like;
phenyl which may be substituted with one or more of halogen, C1-C6 alkyl and C1-C6 alkoxy includes phenyl, 4-chlorophenyl, p-tolyl, o-tolyl and the like; and
tetrahydrofuryl which may be substituted with one or more of hydroxy, C1-C6 alkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy and C1-C6 alkylcarbonyloxy includes 3-tetrahydrofuryl, 4-hydroxy-3-tetrahydrofuryl, 4-methoxy-3-tetrahydrofuryl, 4-acetoxy-3-tetrahydrofuryl and the like.
With regard to R22 and R23, C1-C6 alkyl includes methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, isopentyl, neopentyl, hexyl and the like;
C1-C6 haloalkyl includes fluoromethyl, chloromethyl, bromomethyl, trifluoromethyl, chloroethyl and the like;
C3-C6 alkenyl includes allyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-butenyl, 3-butenyl and the like;
C3-C6 alkynyl includes propargyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 2-butynyl, 3-butynyl and the like; and benzyl which may be substituted with one or more of halogen, C1-C6 alkyl and C1-C6 alkoxy includes benzyl, 4-chlorobenzyl, 4-methylbenzyl and the like.
With regard to R24 and R25, C1-C6 alkyl includes methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, isopentyl, neopentyl, hexyl and the like;
C1-C6 haloalkyl includes fluoromethyl, chloromethyl, bromomethyl, trifluoromethyl, chloroethyl and the like;
C3-C6 alkenyl includes allyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-butenyl, 3-butenyl and the like;
C3-C6 alkynyl includes propargyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 2-butynyl, 3-butynyl and the like;
benzyl which may be substituted with one or more of halogen, C1-C6 alkyl and C1-C6 alkoxy includes benzyl, 4-chlorobenzyl, 4-methylbenzyl and the like; and
phenyl which may be substituted with one or more of halogen, C1-C6 alkyl and C1-C6 alkoxy includes phenyl, 4-chlorophenyl, p-tolyl, o-tolyl and the like.
With regard to R26, C1-C6 alkyl includes methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, isopentyl, neopentyl, hexyl and the like;
C1-C6 haloalkyl includes fluoromethyl, chloromethyl, bromomethyl, trifluoromethyl, chloroethyl and the like;
C3-C6 alkenyl includes allyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-butenyl, 3-butenyl and the like;
C3-C6 alkynyl includes propargyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 2-butynyl, 3-butynyl and the like;
C3-C6 cycloalkyl includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like;
carboxy C1-C6 alkyl includes carboxymethyl, 1-carboxyethyl, 1-carboxy-1-methylethyl and the like;
C1-C6 alkoxycarbonyl C1-C6 alkyl includes methoxycarbonylmethyl, ethoxycarbonylmethyl, 1-methoxycarbonylethyl, 1-methoxycarbonyl-1-methylethyl, 1-ethoxycarbaonylethyl and the like;
C3-C6 alkenyloxycarbonyl C1-C6 alkyl includes allyloxycarbonylmethyl, 1-allyloxycarbonylethyl, 2-allyloxycarbonylethyl, 1-allyloxycarbonyl-1-methylethyl and the like;
C3-C6 alkynyloxycarbonyl C1-C6 alkyl includes propargyloxycarbonylmethyl, 1-propargyloxycarbonylethyl, 2-propargyloxycarbonylethyl, 1-propargyloxycarbonyl-1-methylethyl and the like;
C1-C6 alkoxy C1-C6 alkyl includes 2-methoxyethyl, 2-ethoxyethyl, 3-methoxypropyl and the like;
benzyl which may be substituted with one or more of halogen, C1-C6 alkyl and C1-C6 alkoxy includes benzyl, 4-chlorobenzyl, 4-methylbenzyl and the like; and
phenyl which may be substituted with one or more of halogen, C1-C6 alkyl and C1-C6 alkoxy includes phenyl, 4-chlorophenyl, p-tolyl, o-tolyl and the like.
With regard to R27, C1-C6 alkyl includes methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, isopentyl, neopentyl, hexyl and the like;
C1-C6 haloalkyl includes fluoromethyl, chloromethyl, bromomethyl, trifluoromethyl, chloroethyl and the like;
C3-C6 alkenyl includes allyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-butenyl, 3-butenyl and the like;
C3-C6 alkynyl includes propargyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 2-butynyl, 3-butynyl and the like;
C3-C6 cycloalkyl includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like;
carboxy C1-C6 alkyl includes carboxymethyl, 1-carboxyethyl, 1-carboxy-1-methylethyl and the like;
C1-C6 alkoxycarbonyl C1-C6 alkyl includes methoxycarbonylmethyl, ethoxycarbonylmethyl, 1-methoxycarbonylethyl, 1-methoxycarbonyl-1-methylethyl, 1-ethoxycarbonylethyl and the like;
C3-C6 alkenyloxycarbonyl C1-C6 alkyl includes allyloxycarbonylmethyl, 1-allyloxycarbonylethyl, 2-allyloxycarbonylethyl, 1-allyloxycarbonyl-1-methylethyl and the like;
C3-C6 alkynyloxycarbonyl C1C6 alkyl includes propargyloxycarbonylmethyl, 1-propargyloxycarbonylethyl, 2-propargyloxycarbonylethyl, 1-propargyloxycarbonyl-1-methylethyl and the like;
C1-C6 alkoxy C1-C6 alkyl includes 2-methoxyethyl, 2-ethoxyethyl, 3-methoxypropyl and the like;
benzyl which may be substituted with one or more of halogen, C1-C6 alkyl and C1-C6 alkoxy includes benzyl, 4-chlorobenzyl, 4-methylbenzyl and the like; and
phenyl which may be substituted with one or more of halogen, C1-C6 alkyl and C1-C6 alkoxy includes phenyl, 4-chlorophenyl, p-tolyl, o-tolyl and the like.
With regard to R28, C1-C6 alkyl includes methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, isopentyl, neopentyl, hexyl and the like;
C1-C6 haloalkyl includes fluoromethyl, chloromethyl, bromomethyl, trifluoromethyl, chloroethyl and the like;
C3-C6 alkenyl includes allyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-butenyl, 3-butenyl and the like;
C3-C6 alkynyl includes propargyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 2-butynyl, 3-butynyl and the like;
benzyl which may be substituted with one or more of halogen, C1-C6 alkyl and C1-C6 alkoxy includes benzyl, 4-chlorobenzyl, 4-methylbenzyl and the like; and
phenyl which may be substituted with one or more of halogen, C1-C6 alkyl and C1-C6 alkoxy includes phenyl, 4-chlorophenyl, p-tolyl, o-tolyl and the like.
With regard to R29 and R30, C1-C6 alkyl includes methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, isopentyl, neopentyl, hexyl and the like;
C1-C6 haloalkyl includes fluoromethyl, chloromethyl, bromomethyl, trifluoromethyl, chloroethyl and the like;
C3-C6 alkenyl includes allyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-butenyl, 3-butenyl and the like;
C3-C6 alkynyl includes propargyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 2-butynyl, 3-butynyl and the like; and
benzyl which may be substituted with one or more of halogen, C1-C6 alkyl and C1-C6 alkoxy includes benzyl, 4-chlorobenzyl, 4-methylbenzyl and the like.
With regard to R31, C1-C6 alkyl includes methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, isopentyl, neopentyl, hexyl and the like;
C1-C6 haloalkyl includes fluoromethyl, chloromethyl, bromomethyl, trifluoromethyl, chloroethyl and the like;
C3-C6 alkenyl includes allyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-butenyl, 3-butenyl and the like;
C3-C6 alkynyl includes propargyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 2-butynyl, 3-butynyl and the like;
benzyl which may be substituted with one or more of halogen, C1-C6 alkyl and C1-C6 alkoxy includes benzyl, 4-chlorobenzyl, 4-methylbenzyl and the like; and
phenyl which may be substituted with one or more of halogen, C1-C6 alkyl and C1-C6 alkoxy includes phenyl, 4-chlorophenyl, p-tolyl, o-tolyl and the like.
With regard to R32, C1-C6 alkyl includes methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, isopentyl, neopentyl, hexyl and the like;
C1-C6 haloalkyl includes fluoromethyl, chloromethyl, bromomethyl, trifluoromethyl, chloroethyl and the like;
C3-C6 alkenyl includes allyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-butenyl, 3-butenyl and the like;
C3-C6 alkynyl includes propargyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 2-butynyl, 3-butynyl and the like;
benzyl which may be substituted with one or more of halogen, C1-C6 alkyl and C1-C6 alkoxy includes benzyl, 4-chlorobenzyl, 4-methylbenzyl and the like; and
phenyl which may be substituted with one or more of halogen, C1-C6 alkyl and C1-C6 alkoxy includes phenyl, 4-chlorophenyl, p-tolyl, o-tolyl and the like.
With regard to R33, R34 and R35, C1-C6 alkyl includes methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, isopentyl, neopentyl, hexyl and the like;
C1-C6 haloalkyl includes fluoromethyl, chloromethyl, bromomethyl, trifluoromethyl, chloroethyl and the like;
C3-C6 alkenyl includes allyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-butenyl, 3-butenyl and the like;
C3-C6 alkynyl includes propargyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 2-butynyl, 3-butynyl and the like;
benzyl which may be substituted with one or more of halogen, C1-C6 alkyl and C1-C6 alkoxy includes benzyl, 4-chlorobenzyl, 4-methylbenzyl and the like; and
phenyl which may be substituted with one or more of halogen, C1-C6 alkyl and C1-C6 alkoxy includes phenyl, 4-chlorophenyl, p-tolyl, o-tolyl and the like.
Preferably, A1 is methyl or amino, A2 is C1-C3 alkyl substituted with fluorine, more preferably trifluoromethyl, X is fluorine, Y is chlorine, R2 is hydrogen, R3 is hydrogen, R4 is hydrogen, R5 is hydrogen and R1 is xe2x80x94OR21 (for R21, hydrogen, C1-C6 alkyl, C3-C6 alkenyl or C3-C6 alkynyl are preferred.) or xe2x80x94SR26 (for R26, C1-C6 alkyl, C3-C6 alkenyl or C3-C6 alkynyl are preferred.) from the viewpoint of herbicidal activity.
Processes for producing the present compound will now be explained below. The present compound can be produced, for example, by processes described in [Process 1] to [Process 4] shown below. [Process 1]
A process for producing the present compound from a compound [I] by a production route shown in the following scheme: 
wherein A1, A2, X, Y, R2, R3, R4 and R5 are the same as defined above, R11 represents a group of R1 other than xe2x80x94OH and xe2x80x94SH and L1 represents a leaving group including chlorine, bromine, iodine, methanesulfonyloxy, p-toluenesulfonyloxy and the like.
(Step 1)
The process is carried out by reacting compound [I] with compound [II] in a solvent or without solvent in the presence of a base.
Reaction temperature: xe2x88x9210 to 150xc2x0 C.
Reaction period: a moment to 24 hours
Base material: organic base such as pyridine, triethylamine and the like and inorganic base such as sodium hydroxide, sodium hydride and the like
Amount of base: While the theoretical amount is 1 mole on the basis of 1 mole of the compound [II], the amount thereof can optionally be varied within a range of 1 mole to an excess on the basis of 1 mole of the compound [II] according to the condition of the reaction.
Amount of compound [II] used in the reaction: While the theoretical amount is 1 mole on the basis of 1 mole of the compound [I], the amount thereof can optionally be varied within a range of 1 mole to an excess on the basis of 1 mole of the compound [I] according to the condition of the reaction.
Solvent material: acid amides including N,N-dimethylforamide (hereinafter, referred to as DMF) and the like and hydrocarbons including toluene and the like
After the reaction is completed, the desired compound can be obtained by adding water to the reaction mixture and collecting the produced crystals, or adding water to the reaction mixture and applying the conventional post-treatment such as the extraction with an organic solvent and concentration or the like. The resulting compound can be purified by a treatment such as chromatography, recrystallization and the like.
[Process 2]
A process for producing the present compound from the compound [I] by a production route shown in the following scheme: 
wherein A1, A2, X, Y, R11, R2, R3, R4 and R5 are the same as defined above, L2 represents a leaving group including chlorine, bromine, iodine, methanesulfonyloxy, p-toluenesulfonyloxy and the like and L3 represents a leaving group including chlorine, bromine, iodine, methanesulfonyloxy, p-toluenesulfonyloxy and the like.
(Step 1)
The reaction is carried out by reacting compound [I] with compound [IV] in a solvent or without solvent in the presence of a base.
Reaction temperature: xe2x88x9210 to 150xc2x0 C.
Reaction period: a moment to 24 hours
Base material: organic base such as pyridine, triethylamine and the like and inorganic base such as sodium hydroxide, sodium hydride, potassium carbonate and the like
Amount of base: While the theoretical amount is 1 mole on the basis of 1 mole of the compound [IV], the amount thereof can optionally be varied within a range of 1 mole to an excess on the basis of 1 mole of the compound [IV] according to the condition of the reaction.
Amount of compound [IV] used in the reaction: While the theoretical amount is 1 mole on the basis of 1 mole of the compound [I], the amount thereof can optionally be varied within a range of 1 mole to an excess on the basis of 1 mole of the compound [I] according to the condition of the reaction.
Solvent material: acid amides including DMF and the like, hydrocarbons including toluene and the like and ethers including tetrahydrofuran (hereinafter, referred to as THF) and the like
After the reaction is completed, the desired compound can be obtained by adding water to the reaction mixture and collecting the produced crystals, or adding water to the reaction mixture and applying the conventional post-treatment such as the extraction with an organic solvent and concentration or the like. The resulting compound can be purified by a treatment such as chromatography, recrystallization and the like.
(Step 2)
The reaction is carried out by reacting the compound [III] in a solvent in the presence of a base.
Reaction temperature: xe2x88x9210 to 150xc2x0 C.
Reaction period: a moment to 24 hours
Base material: sodium hydride, potassium t-butoxide and the like
Amount of base: While the theoretical amount is 1 mole on the basis of 1 mole of the compound [III], the amount thereof can optionally be varied within a range of 1 mole to an excess on the basis of 1 mole of the compound [III] according to the condition of the reaction.
Solvent material: acid amides including DMF and the like, hydrocarbons including toluene and the like, ethers including THF and the like and secondary or tertiary alcohols including t-butanol and the like
After the reaction is completed, the desired compound can be obtained by adding water to the reaction mixture and collecting the produced crystals, or adding water to the reaction mixture and applying the conventional post-treatment such as the extraction with an organic solvent and concentration or the like. The resulting compound can be purified by a treatment such as chromatography, recrystallization and the like.
In addition, the process can be performed by continuously carrying out the step 1 and the step 2 without isolating the compound [III].
[Process 3]
A process for producing the present compound from a compound [XXI] by a production route shown in the following scheme: 
wherein A1, A2, X, Y, R1, R2, R3, R4 and R5 are the same as defined above, L6 represents chlorine or bromine, R54 represents methoxy, ethoxy, t-butoxy, allyloxy or benzyloxy and R55 represents a group of R1 other than xe2x80x94OH.
(Step 1)
The reaction is carried out by hydrolyzing the ester moiety of the compound [XXI].
Specifically, the compound [XXII] can be produced, for example, by heating the compound [XXI] in concentrated hydrochloric acid or, when R54 is benzyloxy, by treating the compound [XXI] in a hydrogen atmosphere in the presence of a Pd/c catalyst.
(Step 2)
The reaction is carried out by reacting the compound [XXII] with thionyl chloride or thionyl bromide.
(Step 3)
The reaction is carried out by reacting the compound [XXIII] with a compound of the formula
Hxe2x80x94R55
in the presence of a base such as pyridine, triethylamine or the like.
[Process 4]
A process for producing the present compound from a compound [VII] by a production route shown in the following scheme: 
wherein A1, A2, X, Y, R11, R2, R3, R4 and R5 are the same as defined above, L4 represents a leaving group including chlorine, bromine, iodine, methanesulfonyloxy, p-toluenesulfonyloxy, 2,4-dinitrophenoxy and the like and R51 represents C1-C5 alkyl (methyl, ethyl, isopropyl, t-butyl and the like) or benzyl.
(Step 1)
The reaction is carried out by reacting the compound [VII] with phosgene.
(Step 2)
The reaction is carried out by reacting the isocyanate compound [VIII] with the compound [X] in the presence of a base.
The compound [IX] can also be produced according to a process described in [Process 5] below.
(Step 3)
The reaction is carried out by reacting the compound [IX] with a compound [XI] in the presence of a base.
[Process 5]
A process for producing the compound [IX] from a compound [VII] by a production route shown in the following scheme: 
wherein A2, X, Y, R11, R51, R2, R3, R4 and R5 are the same as defined above, L5 represents chlorine, bromine or C1-C5alkoxy (methoxy, ethoxy, isopropoxy and the like) and R52 represents C1-C5 alkyl (methyl, ethyl, isopropyl, t-butyl and the like) or benzyl.
(Step 1)
The reaction is carried out by reacting the compound [VII] with the compound [XIV] in a solvent or without solvent in the presence of a base.
Reaction temperature: xe2x88x9215 to 150xc2x0 C.
Reaction period: a moment to 24 hours
Base material: tertiary amine such as pyridine, triethylamine and the like
Amount of base: While the theoretical amount is 1 mole on the basis of 1 mole of the compound [VII], the amount thereof can optionally be varied within a range of 1 mole to an excess on the basis of 1 mole of the compound [VII] according to the condition of the reaction.
Amount of compound [XIV] used in the reaction: While the theoretical amount is 1 mole on the basis of 1 mole of the compound [VII], the amount thereof can optionally be varied within a range of 1 mole to an excess on the basis of 1 mole of the compound [VII] according to the condition of the reaction.
Solvent material: hydrocarbons including toluene, xylene and the like, acid amides including DMF and the like and ethers including THF, dioxane and the like
After the reaction is completed, the desired compound can be obtained by adding water to there action mixture and collecting the produced crystals, or adding water to the reaction mixture and applying the conventional post-treatment such as the extraction with an organic solvent and concentration or the like. The resulting compound can be purified by a treatment such as chromatography, recrystallization and the like.
(Step 2)
The reaction is carried out by reacting the compound [XV] with the compound [X] in a solvent or without solvent in the presence of a base.
Reaction temperature: xe2x88x9215 to 150xc2x0 C.
Reaction period: a moment to 24 hours
Base material: inorganic base including sodium hydride, sodium hydroxide, potassium t-butoxide and the like
Amount of base: While the theoretical amount is 1 mole on the basis of 1 mole of the compound [XV], the amount thereof can optionally be varied within a range of 1 mole to an excess on the basis of 1 mole of the compound [XV] according to the condition of the reaction.
Amount of compound [X] used in the reaction: While the theoretical amount is 1 mole on the basis of 1 mole of the compound [XV], the amount thereof can optionally be varied within a range of 1 mole to an excess on the basis of 1 mole of the compound [XV] according to the condition of the reaction.
Solvent material: hydrocarbons including toluene, xylene and the like, acid amides including DMF and the like and ethers including THF, dioxane and the like
After the reaction is completed, the desired compound can be obtained by adding water to there action mixture and collecting the produced crystals, or adding water to the reaction mixture and applying the conventional post-treatment such as the extraction with an organic solvent and concentration or the like. The resulting compound can be purified by a treatment such as chromatography, recrystallization and the like.
The compound [VII] can be produced according to processes described in [Process 6] and [Process 7] below.
[Process 6]
A process for producing the compound [VII] from a compound [XVI] by a production route shown in the following scheme: 
wherein X, Y, R11, R2, R3, R4, R5, L2 and L3 are the same as defined above.
The process can be carried out according to the process described in Process 2 by using the compound [XVI] in place of the compound [I].
[Process 7]
A process for producing the compound [VII] from a compound [XVIII] by a production route shown in the following scheme: 
wherein X, Y, R11, R2, R3, R4, R5, L2 and L3 are the same as defined above.
(Step 1) and (Step 2)
The reactions can be carried out according to the process described in Process 2 by using the compound [XVIII] in place of the compound [I]
(Step 3)
The reaction can be carried out by reducing the compound [XX] with a reducing agent such as iron powder.
The compound [I] can be produced according to processes described in U.S. Pat. No. 4,859,229, JP 11-508543A, JP 11-500714A, JP 11-510145A or WO 98/41093.
The compound [XVI] and the compound [XVIII] can be produced according to a process described EP 61741 A.
The present compounds have excellent herbicidal activity and some of them can exhibit excellent selectivity between crops and weeds. In other words, the present compounds have herbicidal activity against various weeds which may cause some trouble in the foliar treatment and soil treatment on upland fields, such as listed below.
Onagraceous weeds:
large-flowered eveningprimrose (Oenothera erythrosepala), Common eveningprimrose (Oenothera biennis), cutleaf eveningprimrose (Oenothera laciniata),
Ranunculaceous weeds:
roughseeded buttercup (Ranunculus muricatus), hairy buttercup (Ranunculus sardous)
Polygonaceous weeds:
wild buckwheat (Polygonum convolvulus), pale smartweed (Polygonum lapathifolium), pennsylvania smartweed (Polygonum pensylvanicum) ladysthumb (Polygonum persicaria), curly dock (Rumex crispus), broadleaf dock (Rumex obtusifolius), Japanese knotweed (Polygonum cuspidatum), Prostrate knotweed (Polygonum aviculare), red sorrel (Rumex acetosella)
Portulacaceous weeds:
common purslane (Portulaca oleracea)
Caryophyllaceous weeds:
common chickweed (stellaria media), sticky chickweed (Cerastium glomeratum)
Chenopodiaceous weeds:
common lambsquarters (Chenopodium album), kochia (Kochia scoparia)
Amaranthaceous weeds:
redroot pigweed (Amaranthus retroflexus), smooth pigweed (Amaranthus hybridus), palmer amaranth (Amaranthus palmeri), tall waterhemp (Amaranthus tuberculatus), common waterhemp (Amaranthus rudis)
Cruciferous (brassicaceous) weeds:
wild radish (Raphanus raphanistrum), wild mustard (Sinapis arvensis), shepherdpurse (Capsella bursa-pastoris), virginia pepperweed (Lepidium virginicum)
Leguminous (fabaceous) weeds:
hemp sesbania (Sesbania exaltata), sicklepod (Cassia obtusifolia), Florida beggarweed (Desmodium tortuosum), white clover (Trifolium repens), common vetch (Vicia sativa), black medik (Medicago lupulina)
Papaveraceous weeds
Common poppy (Papaver rhoeas)
Malvaceous weeds:
velvetleaf (Abutilon theophrasti), pricklysida (Sida spinosa), venice mallow (Hibiscus trionum)
Violaceous weeds:
field pansy (Viola arvensis), wild pansy (Viola tricolor)
Rubiaceous weeds:
catchweed bedstraw (cleavers) (Galium aparine)
Convolvulaceous weeds:
ivyleaf morningglory (Ipomoea hederacea), tall morningglory (Ipomoea purpurea), entireleaf morningglory (Ipomoea hederacea var. integriuscula), pitted morningglory (Ipomoea lacunosa), field bindweed (Convolvulus arvensis), hedge bindweed (Calystegia sepium)
Labiate weeds:
red deadnettle (Lamium purpureum), henbit (Lamium amplexicaule)
Solanaceous weeds:
jimsonweed (Datura stramonium), black nightshade (Solanum nigrum), Horsenettle (Solanum carolinense)
Scrophulariaceous weeds:
birdseye speedwell (Veronica persica) corn speedwell (Veronica arvensis), ivyleaf speedwell (Veronica hederaefolia)
Composite weeds:
common cocklebur (Xanthium pensylvanicum), common sunflower (Helianthus annuus), wild camomille (Matricaria chamomilla), scentless chamomile (Matricaria perforata or inodora), corn marigold (Chrysanthemum segetum), pineappleweed (Matricaria matricarioides), common ragweed (Ambrosia artemisiifolia), giant ragweed (Ambrosia trifida), horseweed (Erigeron canadensis), Japanese mugwort (Artemisia princeps), tall goldenrod (Solidago altissima), late goldenrod (Solidago gigantea), common dandelion (Taraxacum officinale), Common groundsel (Senecio vulgaris), Hairy galinsoga (Galinsoga ciliata)
Boraginaceous weeds:
forget-me-not (Myosotis scorpioides), field forget-me-not (Myosotis arvensis)
Asclepiadaceous weeds:
common milkweed (Asclepias syriaca)
Euphorbiaceous weeds:
sun spurge (Euphorbia helioscopia), spotted spurge (Euphorbia maculata)
Geraniaceous weeds:
Carolina geranium (Geranium carolinianum)
Oxalidaceous weeds:
pink woodsorrel (Oxalis corymbosa)
Cucurbitaceous weeds:
burcucumber (Sicyos angulatus)
Graminaceous weeds:
barnyardgrass (Echinochloa crus-galli), green foxtail (Setaria viridis), giant foxtail (Setaria faberi), large crabgrass (Digitaria sanguinalis), Southern Crabgrass (Digitaria ciliaris), goosegrass (Eleusine indica), annual bluegrass (Poa annua), blackgrass (Alopecurus myosuroides), wild oat (Avena fatua), Silky bentgrass (Apera spica-venti), johnsongrass (Sorghum halepense), quackgrass (Agropyron repens), downybrome (Bromus tectorum), bermudagrass (Cynodon dactylon), fall panicum (Panicum dichotomiflorum), Texas panicum (Panicum texanum), shattercane (Sorghum vulgare), woolly cupgrass(Eriochloa villosa), water foxtail (Alopecurus geniculatus)
Commelinaceous weeds:
common dayflower (Commelina communis), tropical spiderwort (Commelina benghalensis)
Equisetaceous weeds:
field horsetail (Equisetum arvense)
Cyperaceous weeds:
rice flatsedge (Cyperus iria), purple nutsedge (Cyperus rotundus), yellow nutsedge (Cyperus esculentus)
Furthermore, some of the present compounds exhibit no significant phytotoxicity on the main crops including corn (Zea mays), wheat (Triticum aestivum), barley (Hordeum vulgare), rye (Secale cereale), oat (Avena sativa), rice (Oryza sativa), sorghum (Sorghum bicolor), soybean (Glycine max), cotton (Gossypium spp.), sugar beet (Beta vulgaris), peanut (Arachis hypogaea), sunflower (Helianthus annuus), and canola (Brassica napus); and horticultural crops such as flowers, ornamental plants, and vegetable crops.
The present compounds can also attain effective control of various weeds which can cause trouble in the no-tillage cultivation of soybean (Glycine max), corn (Zea mays), wheat (Triticum aestivum), and other crops. Furthermore, some of the present compounds exhibit no significant phytotoxicity on the crops.
The present compounds also have herbicidal activity against various weeds which may cause some trouble in flooding treatment of paddy fields, such as listed below.
Graminaceous weeds:
barnyardgrass (Echinochloa oryzicola)
Scrophulariaceous weeds:
common false pimpernel (Lindernia procumbens), low false pimpernel (Lindernia dubia var. major), moist bank pimpernel (Lindernia dubia var.dubia), yellow-seed false pimpernel (Lindernia anagallidea), Lindelnia (Lindernia micrantha), suzumenotougarashi (Lindernia antipoda)
Lythraceous weeds:
Indiantoothcup (Rotala indica), red stem (Ammannia multiflora), valley redstem (Ammannia coccinea)
Elatinaceous weeds:
waterwort (Elatine triandra)
Cyperaceous weeds:
smallflower umbrella sedge (Cyperus difformis), hardstem bulrush (Scirpus juncoides subsp. hotarui), inu-hotarui (Scirpus juncoides subsp. juncoides), needle spikerush (Eleocharis acicularis), water nutgrass (Cyperus serotinus), water chestnut (Eleocharis kuroguwai)
Pontederiaceous weeds:
monochoria (Monochoria vaginalis)
Alismataceous weeds:
arrowhead (Sagittaria pygmaea), arrowhead (Sagittaria trifolia), waterplantain (Alisma canaliculatum)
Potamogetonaceous weeds:
roundleaf pondweed (Potamogeton distinctus)
Umbelliferous weeds:
watercelery sp. (Oenanthe javanica)
Furthermore, some of the present compounds exhibit no significant phytotoxicity on transplanted paddy rice.
The present compounds can also be used to control a wide variety of weeds which are growing or will grow in other non-cultivated lands in which weed controlling is necessiated such as a levee, riverbed, roadside, railroad, green field area of a park, ground, parking area, airport, industrial place (ex. factory, storage equipment), fallow land, vacant lot, orchards, grasslands, lawns, forests, and the like. The present compounds also have herbicidal activity against various aquatic weeds, such as water hyacinth (Eichhornia crassipes), which are growing or will grow at the waterside such as rivers, canals, waterways or reservoirs.
Furthermore, where crops with tolerance imparted by introducing a herbicide tolerance gene as described in WO 95/34659 are cultivated, the present compounds can be used at larger rates than those used when ordinary crops without tolerance are cultivated, which makes it possible to control other unfavorable weeds more effectively.
When the present compounds are used as the active ingredients of herbicides, they may be suitably mixed with solid or liquid carriers or diluents, surfactants, and other auxiliary agents to give emulsifiable concentrates, wettable powders, flowables, granules, concentratedemulsions, water-dispersible granules, or other formulations.
These formulations may contain any of the present compounds as an active ingredient at an amount of about 0.001 to about 80% by weight, preferably about 0.005 to about 70% by weight, based on the total weight of the formulation.
Solid carriers for use in the present invention include, fine powders of mineral matters such as kaolin clay, attapulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, and calcite; fine powders of organic substances such as walnut shell powder; fine powders of water-soluble organic substances such as urea; fine powders of inorganic salts such as ammonium sulfate; and fine powders of synthetic hydrated silicon oxide. Liquid carriers for use in the present invention include, aromatic hydrocarbons such as methylnaphthalene, phenylxylylethane, and alkylbenzene (e.g., xylene); alcohols such as isopropanol, ethylene glycol, and 2-ethoxyethanol; esters such as phthalic acid dialkyl esters; ketones such as acetone, cyclohexanone, and isophorone; mineral oils such as machine oil; vegetable oils such as soybean oil and cottonseed oil; dimethyl sulfoxide, N,N-dimethylformamide, acetonitrile, N-methylpyrrolidone, water and the like. Other carriers suitable for use in the present invention will be apparent to one skilled in the art.
The surfactant used for emulsification, dispersing, or spreading may include surfactants of the anionic type, such as alkylsulfates, alkylsulfonates, alkylarylsulfonates, dialkylsulfosuccinates, and phosphates of polyoxyethylene alkyl aryl ethers; and surfactants of the nonionic type, such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene polyoxypropylene block copolymers, sorbitan fatty acid esters, and polyoxyethylene sorbitan fatty acid esters. Other surfactants suitable for use in the present invention will be apparent to one skilled in the art.
Other auxiliary agents that may be utilized in the present invention include lignin sulfonates, alginates, polyvinyl alcohol, gum arabic, CMC (carboxymethylcellulose), and PAP (isopropyl acid phosphate). Other auxiliary agents suitable for use in the present invention will be apparent to one skilled in the art.
The present compounds are usually formulated and then used for soil, foliar, or flooding treatment at pre- or post-emergence of weeds. The soil treatment may include soil surface treatment and soil incorporation. The foliar treatment may include application over the plants and directed application in which a chemical is applied only to weeds so as to keep it off the crop plants.
The present compounds may often exhibit the enhancement of herbicidal activity when used in admixture with other herbicides. They can also be used in admixture with in secticides, acaricides, nematocides, fungicides, bactericides, plant growth regulators, fertilizers, and soil conditioners.
The present compounds may, for example, be used in admixture with the following herbicides: atrazine, cyanazine, dimethametryn, metribuzin, prometryn, simazine, simetryn, chlorotoluron, diuron, fluometuron, isoproturon, linuron, methabenzthiazuron, propanil, bentazone, bromoxynil, ioxynil, pyridate, butamifos, dithiopyr, ethalfluralin, pendimethalin, thiazopyr, trifluralin, acetochlor, alachlor, butachlor, diethatyl-ethyl, dimethenamid, fluthiamide, mefenacet, metolachlor, pretilachlor, propachlor, cinmethylin, acifluorfen, acifluorfen-sodium, benzfendizone, bifenox, butafenacil, chlomethoxynil, fomesafen, lactofen, oxadiazon, oxadiargyl, oxyfluorfen, carfentrazone-ethyl, fluazolate, flumiclorac-pentyl, flumioxazine, fluthiacet-methyl, isopropazol, sulfentrazone, thidiazimin, azafenidin, pyraflufen-ethyl, cinidon-ethyl, difenzoquat, diquat, paraquat, 2,4-D, 2,4-DB, clopyralid, dicamba, fluroxypyr, MCPA, MCPB, mecoprop, quinclorac, triclopyr, azimsulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cloransulam-methyl, cyclosulfamuron, diclosulam, ethoxysulfuron, flazasulfuron, flucarbazone, flumetsulam, flupyrsulfuron, halosulfuron-methyl, imazosulfuron, indosulfuron, metosulam, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron-methyl, procarbazone-sodium, prosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron-methyl, sulfosulfuron, triasulfuron, tribenuron-methyl, tritosulfuron, thifensulfuron-methyl, triflusulfuron-methyl, pyribenzoxim, bispyribac-sodium, pyriminobac-methyl, pyrithiobac-sodium, imazameth, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, tepraloxydim, alloxydim-sodium, clethodim, clodinafop-propargyl, cyhalofop-butyl, dichlofop-methyl, fenoxaprop-ethyl, fenoxaprop-p-ethyl, fluazifop-buthyl, fluazifop-p-butyl, haloxyfop-methyl, quizalofop-p-ethyl, sethoxydim, tralkoxydim, diflufenican, flurtamone, norflurazone, benzofenap, isoxaflutole, pyrazolate, pyrazoxyfen, sulcotrione, clomazone, mesotrione, isoxachlortole, bialaphos, glufosinate-ammonium, glyphosate, sulfosate, dichlobenil, isoxaben, benthiocarb, butylate, dimepiperate, EPTC, esprocarb, molinate, pyributicarb, triallate, iflufenzopyr, bromobutide, DSMA, MSMA, cafenstrol, daimron, epoprodan, flupoxam, metobenzuron, pentoxazone, piperophos, triaziflam, beflubutamid, benzobicyclon, clomeprop, fentrazamide, flufenacet, florasulam, indanofan, isoxadifen, mesotrione, naploanilide, oxaziclomefone, pethoxyamid, phnothiol, and pyridafol.
The above compounds are described in the catalog of Farm Chemicals Handbook, 1995 (Meister Publishing Company); AG CHEM NEW COMPOUND REVIEW, VOL. 13, 1995, VOL. 15, 1997, or VOL. 16, 1998 or, AGROW No. 296 p22, No. 297 p21, No. 308 p22, or No. 324 p26-27, or Josouzai Kenkyu Souran (Hakuyu-sha).
When the present compounds are used as the active ingredients of herbicides, the application amount, although it may vary with the weather conditions, formulation types, application times, application methods, soil conditions, crops to be protected, and weeds to be controlled, etc. is preferably in the range of about 0.01 to about 20,000 g, more preferably about 1 to about 12,000 g, per hectare. In the case of emulsifiable concentrates, wettable powders, flowables, concentrated emulsions, water-dispersible granules, or the like, they are usually applied after being diluted in their prescribed amounts with water (if necessary, containing an adjuvant such as a spreading agent) at a ratio of about 10 to about 1000 liters per hectare. In the case of granules or some types of flowables, they are usually applied as such without any dilution.
The adjuvant which can be used, if necessary, may include, in addition to the surfactants as described above, polyoxyethylene resin acids (esters), lignin sulfonates, abietates, dinaphthylmethanedisulfonates, crop oil concentrates, and vegetable oils such as soybean oil, corn oil, cottonseed oil, and sunflower oil. Other adjuvants suitable for use in the present invention will be apparent to one skilled in the art.
The present compounds can also be used as the active ingredients of harvesting aids such as defoliants and desiccants for cotton (Gossipyum spp.), and desiccants for potato (Solanum tuberosum). In these cases, the present compounds are usually formulated in the same manner as when they are used as the active ingredients of herbicides, and may be used alone or in admixture with other harvesting aids for foliar treatment before the harvesting of crops.